Dark Masters
MetalSeadramon
The first Dark Master, he rules over the aquatic portions of Spiral Mountain. A hothead eager to prove himself, he's a cyborg sea serpent with gold plating, and an energy cannon affixed to his snout. He is Mermaimon's master, and with her spellcasting follows, intends to enslave water pokemon and turn humans into his private Burst Warrior slaves.
- Bad Boss: Notably averted, as he's about the only Big Bad in the first series not to be one. So long as you do your job right he's actually a pretty good boss. Yeah, he killed Scorpiomon, but only after he failed him rather severely, and was very willing to reward him with his favorite food for doing his job correctly. That said, he's pretty short-tempered and impatient at best, so he's still pretty evil.
- Breath Weapon: Unlike other Seadramon, he breathes fire instead of ice.
- The Brute: Not The Evil Genius or The Dragon within the Dark Master's group
- Cyborg: "No matter, wherever those kids try to hide, I'll find them. I rule this ocean with an iron hand, iron tail, and an iron everything, for that matter."
- Flight: Either due to jets along his body, or Power Floats.
- Flying Seafood Special: He's metal, so he's not very edible however
- If It Swims, It Flies: See Flight
- Leeroy Jenkins: He prefers not to play with his food, just cook it.
- Light Is Not Good: So far, he's the only purely villainous main antagonist whose attribute has been Data, a type usually attributed to good Digimon.
- Nigh-Invulnerable: "What was that, a love tap? I'm made of Chrome Digizoid too, you know! You can't hurt me that easily!"
- The Nose Knows: "Do you smell something? There's the scent of DigiDestined in the current. Either that, or there's a bad patch of seaweed around here..."
- Only Sane Man: Out of the Big Bad Ensemble of Piedmon, Puppetmon, Machinedramon, and himself, he seems to be the only one who isn't a sadistic psychopath.
- Our Dragons Are Different" He is a "dramon"
- Pitiful Worms: Namely towards his underlings and opponents
- Pragmatic Villainy: He's a pretty much a Benevolent Boss as long as you do your job right
- Sea Monster: He's a giant metal sea dragon.
Puppetmon
The second Dark Master, he rules over the woodlands of Spiral Mountain. A creepy living marionette, he has the personality of a spoiled brat, and an explosive temper. Is plotting with Petermon in manipulating children to leave their homes and come to Never Never Land.
- Bad Boss: A VERY bad boss indeed, having a habit of killing off henchmen for fun.
- Battle Boomerang: He uses his cross as one to kill
- Beware the Silly Ones: He's goofy, fun-loving... and pretty damn sadistic and cruel.
- Carry a Big Stick: The wooden cross on his back can be detached and wielded as a weapon.
- Creepy Child: It helps (or rather doesn't) that he has a natural Kubrick Stare caused by his hat.
- Double Weapon: His hammer is also a gatling gun-like energy weapon.
- Giggling Villain: Taken to truly creepy levels in his image song.
- Glowing Eyes of Doom: When he transformed his mansion into a Humongous Mecha.
- Kick the Dog: Being the nasty little kid he is, he loves to do this.
- Kubrick Stare: Has a natural one caused by his hat
- Lack of Empathy: Implied, but not outright stated, to be why he enjoys torturing and killing his playmates. A sympathetic example in some ways, as he truly does want friends but this makes it impossible for him to have true ones.
- Noodle Incident: "This is more fun than the time I was fumigated for termites!"
- Not-So-Harmless Villain: Pretty powerful, for something that looks like a child's toy. He's a Mega!
- Pintsized Powerhouse: He's about the same size as T.K.
- Psychopathic Manchild: Type C or E, or a combination of both.
- Sinister Schnoz
- Sinister Surveillance: In the first episode of his arc he uses a television with a remote control to spy on (and mess around with) the kids.
Machinedramon
"Oh good, just what I was looking for - victims."
The third Dark Master, he rules over the industrial areas of Spiral Mountain. Initially appearing to be just a mindless mechanical monstrosity, he turns out to be highly intelligent, and as cruel as he is efficient. Datamon was one of his minions and while the robotic digimon became The Starscream, Machinedramon's empire is using Datamon's technology to continue turning pokemon into robots.
- Ax-Crazy: Despite his Creepy Monotone voice, he's no less unstable and insane than Puppetmon and Piedmon and some of his lines outright state he enjoys what he does. He also sometimes gets a little carried away. During the final battle with him, he started firing randomly in all directions despite the fact he'd already knocked out the Digimon attacking him, leveling a large part of the city.
- Bad Boss: He constantly belittles his lackeys.
- The Berserker: Once he starts shooting, its really hard for him to stop.
- The Chessmaster: When he's not mindlessly destroying things, Machinedramon proves himself quite capable of outwitting Izzy and Tai.
- City of Everywhere: His domain.
- Creepy Monotone: Speaks very quietly despite his size.
- Deadpan Snarker: Good lord! One of the biggest snarkers in the show. It frequently happens when his minions act stupid and considering that he's the least talkative of the Dark Masters, that's speaking volumes.
- Dynamic Entry: He likes bursting through things.
- Genius Bruiser: He's the largest of the Dark Masters with a massive amount of fire power, but also a skilled strategist.
- Lightning Bruiser: He's surprisingly fast for his size.
- Mix-and-Match Man: He is composed of random pieces of other mechanical Digimon.
- Our Dragons Are Different: A large, wingless mechanical dragon.
- Out of the Inferno: Shrugging off Meteor Wing, Hand of Faith, Celestial Arrow, and Lightning Blade.
- Soft-Spoken Sadist: Never raises his voice beyond a cold, raspy whisper even when he's promising to kill someone in the most painful way he can.
Piedmon
The final Dark Master and the leader of the quartet, he rules over the rest of Spiral Mountain, which consists of portions of the Digital World corrupted and rendered barren by darkness. A clown with vast magical abilities, his demeanor is not too dissimilar The Joker.
- Big Bad: The last of the Dark Masters Arc, and also the strongest Dark Master.
- The Dragon: To Apocalymon, as a result.
- Best for Last: This actually backfired, since the DigiDestined got a lot stronger beating the other Dark Masters while Piedmon stayed the same.
- Forced Transformation: What kind of sicko turns people into keychains!?
- Large Ham: Frequently talks about the war against the DigiDestined as if it were a stage production. Not that it makes him any less terrifying.
- Laughably Evil: Despite being a sadistic monster, he is also very amusing.
- Living Doll Collector: He turns almost everyone into keychains, and cracks jokes about how he's Gotta Catch Them All.
- New Powers as the Plot Demands: His Clown Trick attack, which basically does whatever the plot needs it to.
- Pass the Popcorn: Watching the DigiDestined battle the other Dark Masters.
- Throwing Your Sword Always Works: He throws his swords more often than actually fighting with them.
Deep Savers
Mermaimon
Metal Seadramon's underling, a mermaid sea pirate who leads a crew of aquatic digimon. She was sent to Pokearth with her follows to ensure the Digidestined never returns to the Digital World or their own world, however ended up plotting her own goals. however, unlike Datamon, never tried to be The Starscream but seek out goals to support her masters. They terrorized the Whirl Islands seeking Manaphy's egg, wanting his power to control all water pokemon, and merging the brainwashed become with humans like in Pokemon Reburst, would have been able to enslave humans too.- Fusion Dance: Using the Burst Hearts from Pokemon Reburst, had an army of Water-Type Burst Warriors. Had a special one to use herself with a baby Lugia.
- Pirate Girl: Captain of her own crew
- The Dragon: To Metal Seadramon
- The Rival: To Captain Hookmon
- Why Did It Have to Be Snakes?: Fear of frogs, hates it when they touch her. Captain Hookmon's Geckomon took advantage of that
Witchmon & Sorcerymon
Mermaimon's First and Second Mate, a spellcasting Brother–Sister Team, both specialize in water magic.- An Ice Person: Sorcerymon
- Blow You Away: Witchmon
- Brother–Sister Team: They're siblings
- Catfight: Witchmon... with MISTY!
- Co-Dragons: Both to Mermaimon
- Evil Genius: Sorcerymon
- Making a Splash: Both
- The Rival: Its hinted that Witchmon is the one who got Wizardmon beat up and cast him into the desert before Gatomon found him.
